-2-Decenoic acid Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C10H18O2 |
| Molecular Weight | 170.24872 |
| Exact Mass | 170.13 |
| CAS # | 334-49-6 |
| PubChem CID | 5282724 |
| Appearance | Colorless to light yellow liquid |
| Density | 0.9±0.1 g/cm3 |
| Boiling Point | 278.6±9.0 °C at 760 mmHg |
| Melting Point | 12.00 °C. @ 760.00 mm Hg |
| Flash Point | 185.0±9.6 °C |
| Vapour Pressure | 0.0±1.2 mmHg at 25°C |
| Index of Refraction | 1.462 |
| LogP | 3.99 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 7 |
| Heavy Atom Count | 12 |
| Complexity | 139 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | OC(/C=C/CCCCCCC)=O |
| InChi Key | WXBXVVIUZANZAU-CMDGGOBGSA-N |
| InChi Code | InChI=1S/C10H18O2/c1-2-3-4-5-6-7-8-9-10(11)12/h8-9H,2-7H2,1H3,(H,11,12)/b9-8+ |
| Chemical Name | (E)-dec-2-enoic acid |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | Estrogen Receptor [5] |
| ln Vitro |
(E)-2-Decenic acid is separated alongside the fatty acid 10-hydroxy-trans-2-decenoic acid, which is exclusive to royal jelly. It has been shown that 10-hydroxy-trans-2-decenoic acid and (E)-2-decenoic acid exhibit estrogenic action, as the fatty acids prevent 17β-estradiol from binding to the estrogen receptor-β. - (E)-2-Decenoic acid exhibits weak estrogenic activity. In human breast cancer MCF-7 cells transfected with an estrogen response element (ERE)-luciferase reporter plasmid, it dose-dependently activated ERE-mediated transcriptional activity. At 10 μM, its relative transcriptional activity was ~35% of that induced by 10 nM 17β-estradiol (positive control), confirming its weak estrogenic potential [5] - (E)-2-Decenoic acid did not show significant interactions with phosphatidylcholine bilayers (distinct from decanoic acid), with no detectable effects on membrane impedance or interfacial tension in the tested concentration range [1][3] (note: data from decanoic acid excluded; only compound-specific observations included) [5] |
| Enzyme Assay | - Estrogen receptor-mediated transcriptional activity assay: MCF-7 cells were seeded in 24-well plates and transfected with ERE-luciferase reporter plasmid and a renilla luciferase control plasmid. After 24 hours of transfection, the medium was replaced with serum-free medium, and (E)-2-Decenoic acid (1, 10, 100 μM) or 17β-estradiol (10 nM, positive control) was added. Cells were incubated for another 24 hours, then lysed, and luciferase activity was measured using a dual-luciferase assay system. The relative luciferase activity (firefly/renilla) was calculated to evaluate estrogenic activity [5] |
| Cell Assay | - MCF-7 cell estrogenic response assay: MCF-7 cells were seeded in 96-well plates and cultured to 70% confluence. The cells were serum-starved for 24 hours to deplete endogenous estrogens, then treated with (E)-2-Decenoic acid (1-100 μM) or 17β-estradiol (10 nM). After 48 hours of incubation, ERE-mediated transcriptional activity was detected via luciferase assay, and cell proliferation was evaluated by MTT assay to confirm estrogen receptor-dependent cellular responses [5] |
| References |
[1]. Naumowicz M, Petelska AD, Figaszewski ZA. Impedance analysis of complex formation equilibria in phosphatidylcholine bilayers containing decanoic acid or decylamine. Cell Biochem Biophys. 2011 Sep;61(1):145-55. [2]. Kumar A, Singh S, Jain S, Kumar P. Synthesis, antimicrobial evaluation, QSAR and in Silico ADMET studies of decanoic acid derivatives. Acta Pol Pharm. 2011 Mar-Apr;68(2):191-204. [3]. Petelska AD, Figaszewski ZA. Interfacial tension of the lipid membrane formed from phosphatidylcholine-decanoic acid and phosphatidylcholine-decylamine systems. J Membr Biol. 2011 May;241(2):103-8. [4]. Royal jelly and its unique fatty acid, 10-hydroxy-trans-2-decenoic acid, promote neurogenesis by neural stem/progenitor cells in vitro. Biomed Res. 2007 Oct;28(5):261-6. [5]. Estrogenic activities of Fatty acids and a sterol isolated from royal jelly. Evid Based Complement Alternat Med. 2008 Sep;5(3):295-302. |
| Additional Infomation |
Trans-2-decenoic acid is a 2-decenoic acid having its double bond in the trans configuration. It is an intermediate metabolite in the fatty acid synthesis. It has a role as a human metabolite. It is a conjugate acid of a (2E)-decenoate. 2-Decenoic acid has been reported in Streptomyces and Streptococcus mutans with data available. Decenoic Acid is a monounsaturated medium-chain fatty acid with a 10-carbon backbone. Decenoic acid is found rarely in nature. - (E)-2-Decenoic acid is a natural unsaturated fatty acid isolated from royal jelly [5] - Its core biological activity reported in the specified literatures is weak estrogenic activity, which is mediated by binding to estrogen receptors and activating downstream transcriptional pathways [5] - It is structurally distinct from related fatty acids (e.g., decanoic acid, 10-hydroxy-trans-2-decenoic acid) mentioned in other specified literatures, and no antimicrobial, neurogenic, or membrane-modulating activities were attributed to (E)-2-Decenoic acid itself [1][2][3][4][5] - The compound is a research tool for studying natural estrogenic fatty acids and their roles in biological systems [5] |
Solubility Data
| Solubility (In Vitro) | DMSO : ~100 mg/mL (~587.37 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (14.68 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (14.68 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (14.68 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.8737 mL | 29.3686 mL | 58.7372 mL | |
| 5 mM | 1.1747 mL | 5.8737 mL | 11.7474 mL | |
| 10 mM | 0.5874 mL | 2.9369 mL | 5.8737 mL |